When I started playing, early 60s, there were no such thing as wire wound / round wound strings, only tape wound strings, now called flats and I hated them. No brightness at all but then bass was not supposed to sound bright, only bassy.
Then wire wound strings appeared and suddenly there was tone and I used them straight away but still wasn't totally happy, the bottom E always seemed to have too many overtones and was always floppy in that the note would be slightly sharp and then settle down to the right note. This was with the most heavy string available, 45-105. I suspected that the second problem was me 'digging in' but if you're getting into it and performing it's impossible not to play hard, for me anyway and still is.
A few years ago I discovered heavier gauge strings, 50-110 and gave them a try and suddenly I had a proper note and no floppiness on the E string and here I've stayed. Newtone strings are now my string of choice, 50-110, and I'm a happy chappie and it's far to late to try to change my style and how can you possibly do a windmill lightly.
I still hate tape wound strings / flats with a vengeance and just can't understand why anyone would choose them but that's just me.
Sorry for the ramble but that's my string story.